Complex compounds having a ligand containing an N donor and a P donor and the use thereof in the opto-electronic field

Abstract

The invention describes electronic devices comprising a metal complex compound having at least one ligand containing an N donor and a P donor having the formula (I), in which the carbons C1 and C2 are part of an aromatic or non-aromatic ring system F1, P and N are phosphorus and nitrogen, where the nitrogen is in sp2-hybridized form, the radicals R3 and R4 are, independently of one another, hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical having up to 40 C atoms, and R1 and R2 are, independently of one another, an atom or radical from the group comprising hydrogen, halogen, R, RO—, RS—, RCO—, RCOO—, RNH—, R2N—, RCONR— and —Si(R)X(OR)3-X, where R=an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical having up to 40 C atoms and X=1, 2 or 3. The invention furthermore describes a process for the production of an electronic device of this type and processes for the generation of light or blue emission using a metal complex compound of this type.

The invention claimed is: 
     
       1. An electronic device comprising a polynuclear metal complex compound having at least one bidentate ligand containing an N donor and a P donor having the formula I 
       
         
           
           
               
               
           
         
       
       in which
 the carbons C 1  and C 2  are part of an aromatic or non-aromatic ring system F 1 ,
 P and N are phosphorus and nitrogen, 
 R 3  and R 4  are, independently of one another, hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical having up to 40 C atoms, and 
 R 1  and R 2  are, independently of one another, an atom or radical from the group comprising hydrogen, halogen, R—, RO—, RS—, RCO—, RCOO—, RNH—, R 2 N—, RCONR— and —Si(R) X (OR) 3-X , where R=an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical having up to 40 C atoms and X=1, 2 or 3. 
 
 
     
     
       2. The device according to  claim 1 , wherein the metal complex compound has up to six metal centres. 
     
     
       3. The device according to  claim 1 , wherein the metal complex compound has two metal centres. 
     
     
       4. The device according to  claim 1 , wherein the metal complex compound contains at least one of the metals Cu or Ag. 
     
     
       5. The device according to  claim 4 , wherein the metal complex compound is in the ionic form and contains, besides a Cu or Ag ion, at least one further metal from the group with Cu, Ag, Au, Pd, Pt, Rh, Ir, Re, Os, Mo, W or Zn. 
     
     
       6. An electronic device comprising a metal complex compound which has the formula II or the formula III 
       
         
           
           
               
               
           
         
       
       in which
 the carbons C 1  and C 2  are part of an aromatic or non-aromatic ring system F 1 , P and N are phosphorus and nitrogen, 
 R 3  and R 4  are, independently of one another, hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical having up to 40 C atoms, and 
 R 1  and R 2  are, independently of one another, an atom or radical from the group comprising hydrogen, halogen, R—, RO—, RS—, RCO—, RCOO—, RNH—, R2N—, RCONR— and —Si(R)X(OR)3-X, where R=an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical having up to 40 C atoms and X=1, 2 or 3,
 M is a metal from the group with Cu, Ag, Au, Pd, Pt, Rh, Ir, Re, Os, Mo, W and Zn and 
 L 1  and L 2  are, independently of one another, a bridging and/or non-bridging ligand. 
 
 
     
     
       7. The device according to  claim 1 , wherein the metal complex compound has the formula IV 
       
         
           
           
               
               
           
         
         in which
 N, P, C 1 , C 2 , R 1  to R 4  and F 1  are defined as in formula I,
 M 1  and M 2 =a metal from the group with Cu, Ag, Au, Pd, Pt, Rh, Ir, Re, Os, Mo, W and Zn (independently of one another) and 
 L 1  and L 2  are, independently of one another, bridging ligands. 
 
 
       
     
     
       8. The device according to  claim 1 , wherein the metal complex compound has a energetic separation (ΔE separation) between the lowest triplet state and the higher singlet state of between 50 cm −1  and 3000 cm −1 . 
     
     
       9. The device according to  claim 1 , wherein the device is selected from the group consisting of an organic electroluminescent device, a light-emitting electrochemical cell, an organic solar cell, an organic field-effect transistor and an organic laser. 
     
     
       10. The device according to  claim 1 , wherein the device comprises the metal complex compound as constituent of an emitter layer, where the proportion of the metal complex in the emitter layer is between 0.1 and 50% by weight. 
     
     
       11. The device according to  claim 1 , wherein the device comprises the metal complex compound as constituent of an absorber layer, where the proportion of the metal complex in the absorber layer is between 30 and 100% by weight. 
     
     
       12. A process for the production of the electronic device according to  claim 1 , which comprises printing a metal complex compound having the at least one ligand of the formula I onto a substrate. 
     
     
       13. A process for the generation of light of a certain wavelength, comprising the step of providing a polynuclear metal complex compound having a ligand of the formula I 
       
         
           
           
               
               
           
         
         in which
 the carbons C 1  and C 2  are part of an aromatic or non-aromatic ring system F 1 ,
 P and N are phosphorus and nitrogen, 
 R 3  and R 4  are, independently of one another, hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical having up to 40 C atoms, and 
 R 1  and R 2  are, independently of one another, an atom or radical from the group comprising hydrogen, halogen, R—, RO—, RS—, RCO—, RCOO—, RNH—, R 2 N—, RCONR— and —Si(R) X (OR) 3-X , where R=an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical having up to 40 C atoms and X=1, 2 or 3. 
 
 
       
     
     
       14. A process for the generation of blue emission which comprises utilizing a polynuclear metal complex compound having a ligand of the formula I 
       
         
           
           
               
               
           
         
       
       in which
 the carbons C 1  and C 2  are part of an aromatic or non-aromatic ring system F 1 ,
 P and N are phosphorus and nitrogen, 
 R 3  and R 4  are, independently of one another, hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical having up to 40 C atoms, and 
 R 1  and R 2  are, independently of one another, an atom or radical from the group comprising hydrogen, halogen, R—, RO—, RS—, RCO—, RCOO—, RNH—, R 2 N—, RCONR— and —Si(R) X (OR) 3-X , where R=an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical having up to 40 C atoms and X=1, 2 or 3.